AR127731A1 - AMPK ACTIVATORS - Google Patents
AMPK ACTIVATORSInfo
- Publication number
- AR127731A1 AR127731A1 ARP220103198A ARP220103198A AR127731A1 AR 127731 A1 AR127731 A1 AR 127731A1 AR P220103198 A ARP220103198 A AR P220103198A AR P220103198 A ARP220103198 A AR P220103198A AR 127731 A1 AR127731 A1 AR 127731A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- independently selected
- halogen
- occurrence
- hydrogen
- Prior art date
Links
- 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 title abstract 5
- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 title abstract 5
- 239000012190 activator Substances 0.000 title abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 10
- 150000002367 halogens Chemical class 0.000 abstract 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 125000001424 substituent group Chemical group 0.000 abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 4
- 125000004404 heteroalkyl group Chemical group 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 3
- 208000035475 disorder Diseases 0.000 abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 2
- 239000000556 agonist Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000007149 gut brain axis pathway Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 210000005027 intestinal barrier Anatomy 0.000 abstract 1
- 230000007358 intestinal barrier function Effects 0.000 abstract 1
- 239000004031 partial agonist Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000002483 superagonistic effect Effects 0.000 abstract 1
- 230000009885 systemic effect Effects 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
La presente divulgación se dirige, al menos en parte, a activadores de la AMPK útiles para el tratamiento de afecciones o trastornos asociados a la AMPK. En algunas realizaciones, la afección o el trastorno está asociado con el eje intestino-cerebro. En algunas realizaciones, la afección o el trastorno está asociado con la infección sistémica y la inflamación por tener una barrera intestinal permeable. En algunas realizaciones, los activadores de la AMPK son compuestos restringidos al intestino. En algunas realizaciones, los activadores de la AMPK son agonistas, super agonistas, agonistas completos o agonistas parciales. Reivindicación 1: Un compuesto o sal farmacéuticamente aceptable de fórmula (1), caracterizado porque: X es -O-, -CH₂- o -CHR⁴-; o X es -CH-, y L¹ está unido a X; Y es -N- o -CR⁶-; R¹, R² y R³ cada uno se seleccionan independientemente, en cada aparición, de halógeno, hidroxilo, alquilo C₁₋₄, -CN y haloalquilo C₁₋₄; cada R⁴ se selecciona independientemente, en cada aparición, entre halógeno, hidroxilo, alquilo C₁₋₄, -CN y haloalquilo C₁₋₄; o dos R⁴ se juntan para formar un enlace o un alquileno C₁₋₂; n se selecciona entre 0, 1, 2, 3 y 4; o se selecciona entre 0, 1, 2, 3 y 4; p se selecciona entre 0, 1 y 2; q se selecciona entre 0, 1, 2, 3 y 4; R⁵ se selecciona entre hidrógeno y alquilo C₁₋₄; R⁶ se selecciona entre hidrógeno, halógeno, alquilo C₁₋₄ y haloalquilo C₁₋₄; L¹ es un enlace o -CH₂-; D se selecciona entre -CO₂R¹¹, -P(O)(OR¹¹)₂, -P(O)R¹¹(OR¹¹), -S(O)₂OH y -L²-K; L² se selecciona entre ˡ-(C(R¹³)₂)ʳ-, ˡ-O(C(R¹³)₂)ʳ-, ˡ-(C(R¹³)₂)ʳO-, ˡ-N(R¹²)(C(R¹³)₂)ₛ-, ˡ-C(O)O-, ˡ-OC(O)-, ˡ-C(O)N(R¹²)-, ˡ-N(R¹²)C(O)-, ˡ-N(R¹²)S(O)₂-, ˡ-S(O)₂N(R¹²)- y heterociclo de 4 a 6 miembros, donde ˡ denota la conexión a K; r se selecciona entre 1, 2 y 3; s se selecciona entre 0, 1, 2 y 3; K se selecciona entre (I) y (II): (I) alquilo C₁₋₁₀ o heteroalquilo C₁₋₁₀, cada uno de los cuales se sustituye opcionalmente con uno a seis sustituyentes independientemente seleccionados entre: halógeno, -OR¹⁴, -SR¹⁴, -N(R¹⁴)₂, -N⁺(R¹⁵)₃, -C(O)R¹⁴, -C(O)OR¹⁴, -OC(O)R¹⁴, -OC(O)N(R¹⁴)₂, -C(O)N(R¹⁴)₂, -N(R¹⁴)C(O)R¹⁴, -N(R¹⁴)C(O)OR¹⁴, -N(R¹⁴)C(O)N(R¹⁴)₂, -N(R¹⁴)S(O)₂(R¹⁴), -S(O)R¹⁴, -S(O)₂R¹⁴, -S(O)₂N(R¹⁴)₂, =O, -CN, -P(O)(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O)₂OH, carbociclo C₃₋₁₀ y heterociclo de 3 a 10 miembros, donde cada carbociclo C₃₋₁₀ y heterociclo de 3 a 10 miembros se sustituye opcionalmente con uno a seis sustituyentes independientemente seleccionados entre halógeno, alquilo C₁₋₆, -OR¹⁴, =O y -S(O)₂OH; y (II) carbociclo C₃₋₁₀ y heterociclo de 3 a 10 miembros, cada uno de los cuales se sustituye opcionalmente con uno a seis sustituyentes independientemente seleccionados entre: halógeno, -OR¹⁴, -SR¹⁴, -N(R¹⁴)₂, -N⁺(R¹⁵)₃, -C(O)R¹⁴, -C(O)OR¹⁴, -OC(O)R¹⁴, -OC(O)N(R¹⁴)₂, -C(O)N(R¹⁴)₂, -N(R¹⁴)C(O)R¹⁴, -N(R¹⁴)C(O)OR¹⁴, -N(R¹⁴)C(O)N(R¹⁴)₂, -N(R¹⁴)S(O)₂(R¹⁴), -S(O)R¹⁴, -S(O)₂R¹⁴, -S(O)₂N(R¹⁴)₂, -P(O)(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O)₂OH, =O, -CN, alquilo C₁₋₁₀ y heteroalquilo C₁₋₁₀, donde cada alquilo C₁₋₁₀ y heteroalquilo C₁₋₁₀ se sustituye opcionalmente con uno a seis sustituyentes independientemente seleccionados entre halógeno, -OR¹⁴, -SR¹⁴, -N(R¹⁴)₂, -N⁺(R¹⁵)₃, -C(O)OR¹⁴, -P(O)(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O)₂OH, S(O)₂R¹⁴ y =O; R¹¹ se selecciona independientemente, en cada aparición, entre hidrógeno, alquilo C₁₋₄ y haloalquilo C₁₋₄; R¹² se selecciona independientemente, en cada aparición entre hidrógeno y alquilo C₁₋₄ opcionalmente sustituido con halógeno, -OH, -NH₂ y -C(O)NH₂; R¹³ se selecciona independientemente, en cada aparición, entre hidrógeno, alquilo C₁₋₄, haloalquilo C₁₋₄ e hidroxialquilo C₁₋₄; cada R¹⁴ se selecciona independientemente, en cada aparición, entre: hidrógeno; alquilo C₁₋₁₀ y heteroalquilo C₁₋₁₀ opcionalmente sustituido con uno a seis sustituyentes independientemente seleccionados entre halógeno, -OR²¹, -SR²¹, -N(R²¹)₂, -N⁺(R¹⁵)₃, -C(O)R²¹, -C(O)OR²¹, -OC(O)R²¹, -OC(O)N(R²¹)₂, -C(O)N(R²¹)₂, -N(R²¹)C(O)R²¹, -P(O)(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O)₂OH, =O y -CN; y carbociclo C₃₋₁₀ y heterociclo de 3 a 10 miembros, donde cada carbociclo C₃₋₁₀ y heterociclo de 3 a 10 miembros se sustituye opcionalmente con uno a seis sustituyentes independientemente seleccionados entre halógeno, alquilo C₁₋₆, -OR²¹, -N⁺(R¹⁵)₃, -S(O)R²¹, -P(O)(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O)₂OH, -S(O)₂R²¹, -S(O)₂N(R²¹)₂, =O y -CN; cada R¹⁵ se selecciona independientemente entre alquilo C₁₋₄; cada R¹⁶ se selecciona independientemente, en cada aparición, entre hidrógeno y alquilo C₁₋₆; cada R²¹ se selecciona independientemente, en cada aparición, entre hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆ y carbociclo C₃₋₆, donde el carbociclo C₃₋₆ se sustituye opcionalmente con uno a seis sustituyentes independientemente seleccionados entre -OH, alquilo C₁₋₆, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆ y =O.The present disclosure is directed, at least in part, to AMPK activators useful for the treatment of AMPK-associated conditions or disorders. In some embodiments, the condition or disorder is associated with the gut-brain axis. In some embodiments, the condition or disorder is associated with systemic infection and inflammation due to having a leaky intestinal barrier. In some embodiments, the AMPK activators are gut-restricted compounds. In some embodiments, the AMPK activators are agonists, super agonists, full agonists, or partial agonists. Claim 1: A pharmaceutically acceptable compound or salt of formula (1), characterized in that: X is -O-, -CH₂- or -CHR⁴-; or X is -CH-, and L¹ is attached to X; Y is -N- or -CR⁶-; R¹, R² and R³ are each independently selected, at each occurrence, from halogen, hydroxyl, C₁₋₄ alkyl, -CN and C₁₋₄ haloalkyl; each R⁴ is independently selected, at each occurrence, from halogen, hydroxyl, C₁₋₄ alkyl, -CN and C₁₋₄ haloalkyl; or two R⁴ come together to form a bond or a C₁₋₂ alkylene; n is selected from 0, 1, 2, 3 and 4; or is selected between 0, 1, 2, 3 and 4; p is selected between 0, 1 and 2; q is selected from 0, 1, 2, 3 and 4; R⁵ is selected from hydrogen and C₁₋₄ alkyl; R⁶ is selected from hydrogen, halogen, C₁₋₄ alkyl and C₁₋₄ haloalkyl; L¹ is a bond or -CH₂-; D is selected from -CO₂R¹¹, -P(O)(OR¹¹)₂, -P(O)R¹¹(OR¹¹), -S(O)₂OH and -L²-K; L² is selected from ˡ-(C(R¹³)₂)ʳ-, ˡ-O(C(R¹³)₂)ʳ-, ˡ-(C(R¹³)₂)ʳO-, ˡ-N(R¹²)(C( R¹³)₂)ₛ-, ˡ-C(O)O-, ˡ-OC(O)-, ˡ-C(O)N(R¹²)-, ˡ-N(R¹²)C(O)-, ˡ- N(R¹²)S(O)₂-, ˡ-S(O)₂N(R¹²)- and 4- to 6-membered heterocycle, where ˡ denotes the connection to K; r is selected between 1, 2 and 3; s is selected from 0, 1, 2 and 3; K is selected from (I) and (II): (I) C₁₋₁₀ alkyl or C₁₋₁₀ heteroalkyl, each of which is optionally substituted with one to six substituents independently selected from: halogen, -OR¹⁴, -SR¹⁴, -N(R¹⁴)₂, -N⁺(R¹⁵)₃, -C(O)R¹⁴, -C(O)OR¹⁴, -OC(O)R¹⁴, -OC(O)N(R¹⁴)₂, -C( O)N(R¹⁴)₂, -N(R¹⁴)C(O)R¹⁴, -N(R¹⁴)C(O)OR¹⁴, -N(R¹⁴)C(O)N(R¹⁴)₂, -N(R¹⁴) S(O)₂(R¹⁴), -S(O)R¹⁴, -S(O)₂R¹⁴, -S(O)₂N(R¹⁴)₂, =O, -CN, -P(O)(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O)₂OH, C₃₋₁₀ carbocycle and 3- to 10-membered heterocycle, where each C₃₋₁₀ carbocycle and 3- to 10-membered heterocycle is optionally substituted with one to six substituents independently selected from halogen, C₁₋₆ alkyl, -OR¹⁴, =O and -S(O)₂OH; and (II) C₃₋₁₀ carbocycle and 3- to 10-membered heterocycle, each of which is optionally substituted with one to six substituents independently selected from: halogen, -OR¹⁴, -SR¹⁴, -N(R¹⁴)₂, -N ⁺(R¹⁵)₃, -C(O)R¹⁴, -C(O)OR¹⁴, -OC(O)R¹⁴, -OC(O)N(R¹⁴)₂, -C(O)N(R¹⁴)₂, - N(R¹⁴)C(O)R¹⁴, -N(R¹⁴)C(O)OR¹⁴, -N(R¹⁴)C(O)N(R¹⁴)₂, -N(R¹⁴)S(O)₂(R¹⁴), -S(O)R¹⁴, -S(O)₂R¹⁴, -S(O)₂N(R¹⁴)₂, -P(O)(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O) ₂OH, =O, -CN, C₁₋₁₀ alkyl and C₁₋₁₀ heteroalkyl, where each C₁₋₁₀ alkyl and C₁₋₁₀ heteroalkyl is optionally substituted with one to six substituents independently selected from halogen, -OR¹⁴, -SR¹⁴, -N (R¹⁴)₂, -N⁺(R¹⁵)₃, -C(O)OR¹⁴, -P(O)(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O)₂OH, S(O )₂R¹⁴ y =O; R¹¹ is independently selected, at each occurrence, from hydrogen, C₁₋₄ alkyl and C₁₋₄ haloalkyl; R¹² is independently selected, at each occurrence, from hydrogen and C₁₋₄ alkyl optionally substituted with halogen, -OH, -NH₂ and -C(O)NH₂; R¹³ is independently selected, at each occurrence, from hydrogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl and C₁₋₄ hydroxyalkyl; each R¹⁴ is independently selected, at each occurrence, from: hydrogen; C₁₋₁₀ alkyl and C₁₋₁₀ heteroalkyl optionally substituted with one to six substituents independently selected from halogen, -OR²¹, -SR²¹, -N(R²¹)₂, -N⁺(R¹⁵)₃, -C(O)R²¹, - C(O)OR²¹, -OC(O)R²¹, -OC(O)N(R²¹)₂, -C(O)N(R²¹)₂, -N(R²¹)C(O)R²¹, -P(O )(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O)₂OH, =O and -CN; and C₃₋₁₀ carbocycle and 3- to 10-membered heterocycle, wherein each C₃₋₁₀ carbocycle and 3- to 10-membered heterocycle is optionally substituted with one to six substituents independently selected from halogen, C₁₋₆ alkyl, -OR²¹, -N⁺ (R¹⁵)₃, -S(O)R²¹, -P(O)(OR¹⁶)₂, -P(O)R¹⁶(OR¹⁶), -S(O)₂OH, -S(O)₂R²¹, -S(O )₂N(R²¹)₂, =O and -CN; each R¹⁵ is independently selected from C₁₋₄ alkyl; each R¹⁶ is independently selected, at each occurrence, from hydrogen and C₁₋₆ alkyl; each R²¹ is independently selected, at each occurrence, from hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ hydroxyalkyl and C₃₋₆ carbocycle, where the C₃₋₆ carbocycle is optionally substituted with one to six substituents independently selected from -OH, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ hydroxyalkyl and =O.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US202163282457P | 2021-11-23 | 2021-11-23 |
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AR127731A1 true AR127731A1 (en) | 2024-02-21 |
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ARP220103198A AR127731A1 (en) | 2021-11-23 | 2022-11-22 | AMPK ACTIVATORS |
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AR (1) | AR127731A1 (en) |
TW (1) | TW202340185A (en) |
WO (1) | WO2023097189A1 (en) |
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UY39222A (en) | 2020-05-19 | 2021-11-30 | Kallyope Inc | AMPK ACTIVATORS |
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AU2011218830B2 (en) * | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
EP3243385B1 (en) * | 2011-02-25 | 2021-01-13 | Merck Sharp & Dohme Corp. | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
BR112014001018A2 (en) * | 2011-07-15 | 2017-01-10 | Shionogi & Co | azabenzimidazole derivative having ampk activation activity |
EP3459949A4 (en) * | 2016-05-20 | 2020-04-08 | Shionogi & Co., Ltd | 5-substituted benzimidazole and 5-substituted azabenzimidazole derivative both having ampk activation effect |
EP4172162A4 (en) * | 2020-06-26 | 2024-08-07 | Kallyope Inc | Ampk activators |
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2022
- 2022-11-21 WO PCT/US2022/080264 patent/WO2023097189A1/en unknown
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WO2023097189A1 (en) | 2023-06-01 |
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